Ganstigmine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Ganstigmine
Accession Number
DB06525
Type
Small Molecule
Groups
Investigational
Description

Ganstigmine is an orally active, geneserine derived, carbamate-based acetylcholinesterase inhibitor developed for the treatment of Alzheimer's disease.

Structure
Thumb
Synonyms
  • Ganstigmine
Product Ingredients
IngredientUNIICASInChI Key
Ganstigmine hydrochloride19OP2S99RQ412044-92-9CVDHRWXJJRBPFA-FKXUWVMKSA-N
Categories
UNII
QRR9SV89XI
CAS number
457075-21-7
Weight
Average: 381.476
Monoisotopic: 381.205241741
Chemical Formula
C22H27N3O3
InChI Key
ZOBDWFRKFSPCRB-UNMCSNQZSA-N
InChI
InChI=1S/C22H27N3O3/c1-5-15-8-6-7-9-18(15)23-21(26)27-16-10-11-19-17(14-16)22(2)12-13-24(3)28-20(22)25(19)4/h6-11,14,20H,5,12-13H2,1-4H3,(H,23,26)/t20-,22-/m0/s1
IUPAC Name
(4aS,9aS)-2,4a,9-trimethyl-2H,3H,4H,4aH,9H,9aH-[1,2]oxazino[6,5-b]indol-6-yl N-(2-ethylphenyl)carbamate
SMILES
CCC1=C(NC(=O)OC2=CC3=C(C=C2)N(C)[C@H]2ON(C)CC[C@@]32C)C=CC=C1

Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
7999041
BindingDB
10970
ChEMBL
CHEMBL121810

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP4.03ALOGPS
logP4.82ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)2.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.04 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.55 m3·mol-1ChemAxon
Polarizability42.45 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylcarbamic acid esters
Direct Parent
Phenylcarbamic acid esters
Alternative Parents
Indoles and derivatives / Dialkylarylamines / 1,2-oxazinanes / Carbamate esters / Oxacyclic compounds / N-organohydroxylamines / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Phenylcarbamic acid ester / Indole or derivatives / Dialkylarylamine / 1,2-oxazinane / Oxazinane / Carbamic acid ester / Organoheterocyclic compound / Oxacycle / N-organohydroxylamine / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Bartolucci C, Siotto M, Ghidini E, Amari G, Bolzoni PT, Racchi M, Villetti G, Delcanale M, Lamba D: Structural determinants of Torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819). J Med Chem. 2006 Aug 24;49(17):5051-8. [PubMed:16913695]
  2. Mazzucchelli M, Porrello E, Villetti G, Pietra C, Govoni S, Racchi M: Characterization of the effect of ganstigmine (CHF2819) on amyloid precursor protein metabolism in SH-SY5Y neuroblastoma cells. J Neural Transm (Vienna). 2003 Aug;110(8):935-47. [PubMed:12898348]

Drug created on March 19, 2008 10:35 / Updated on June 04, 2019 06:25